CS245775B2 - Agent for suppresing of weed and/or for desinfection and/or for defoliation of cotton-plants and potetoas and production method of effective compound - Google Patents

Description

The present invention relates to a composition for controlling weeds and / or for desiccation and / or defoliation of cotton plants and potatoes, which contains as active ingredient novel phenoxyphenylamino-amino derivatives. The invention further relates to a process for the production of these new active substances and to their use as an active ingredient in weed control and / or desiccating and / or defoliating cotton and potato plants.

Diphenyl ethers having a herbicidal action are known from European patent application no. No. 27,555, U.S. Pat. No. 4,277,624, and U.S. Pat. No. 2,311,638. Furthermore, European Patent Publication No. 351 discloses phenoxyphenylthioalkanecarboxylic acid derivatives having herbicidal activity.

The novel compounds of the present invention correspond to the general formula I

in which

X is hydrogen or chlorine,

R ¹ represents a hydrogen atom, a nitro group or a C 1 -C 4 alkyl group, a C 2 -C 4 alkenyl group, a C 1 -C 4 alkylcarbonyl group optionally substituted by at least one halogen atom or an alkenylcarbonyl group 2 to 4 carbon atoms in the alkenyl moiety,

Q represents a straight or branched aliphatic radical having 1 to 5 carbon atoms of the formula

~ Á 1 1 G 1 4 1 1 - o -σ- - C ' -ο- • c · 1 ι 1 ι 1 _AND'_ .EÍ b G ^? Ld К

in which

A \ E ', G \ l ^t and M' are hydrogen or alkyl having 1 to 4 carbon atoms or two adjacent substituents A ', E', G ', L' and M 'are also a bond between the two carbon atoms, to which they are bound, A, E, G, L and M are hydrogen or one

Or two of A, E, G, L and M are also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl or -OR ⁵ , -SR ^6, or - COOR ⁷ substituted C 1 -C 4 alkyl, wherein

R ² and R ⁵ are hydrogen,

R ³ and R ⁶ are C 1 -C 4 alkyl, and

R ⁴ and R ⁷ are hydrogen or C 1 -C 4 alkyl, a, b, c and d are 0 or 1, or R ¹ and G are together a trimethylene bridge and a, b, c and d are 0, and

Z represents —COO OO Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or cyano, wherein:

Me © means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfoxonium cation,

R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with halogen, C 1 -C 4 alkoxy, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl ,

R ⁹ represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 3 -C 6 cycloalkyl group and

R ¹⁰ is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally monosubstituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylaminocarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, wherein in compounds wherein R ¹ is hydrogen simultaneously and a, b, c and d are 0, i) G is -OR ² , -COOR ⁴ or C 1 -C 4 alkyl alkyl which is substituted by oR ^5, - SR ⁶ or -COOR ^7, or ii) the G and G 'are both alkyl of 1 to 4 carbon atoms.

C 1 -C 4 alkyl as a substituent or part of a substituent means methyl, ethyl, n-propyl, isobutyl.

C 1 -C 4 alkoxy means methoxy, ethoxy, nisopropyl, n-butyl, sec-butyl, tert-butyl and -propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy and isobutoxy.

Alkenyl and alkenyl groups as substituents or as part of a substituent are to be understood, depending on the number of carbon atoms indicated, for the straight and branched corresponding radicals.

C 3 -C 6 -cycloalkyl means cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

As the Me® cation, an ammonium cattont, a metal cation, an organic nitrogen base, a sulfonyl cation or a sulfoxonium cation are suitable.

Suitable metals for forming salts are alkaline earth metals such as magnesium or calcium, but especially alkali metals such as lithium, potassium, and especially sodium. In addition, transition metals such as iron, nickel, cobalt, copper, zinc, chromium or manganese are also suitable for salt formation.

Examples of organic nitrogen bases suitable for salt formation include primary, secondary and tertiary, aliphatic and aromatic, optionally hydroxylated amines such as methylamine, ethylamine, n-propylamine, isopropylamine, four isomeric butylamines, dimethylamine, diethylamine , di-n-propylamine, diisiopnopylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tri-n-propylamine, clinucline, pyridine, quinoline, isoquinoline, as well as ethanolamine, propanolamine, diethanolamine or triethanolamine or triethylamine and quaternary ammonium tetraoxyl ammonium oxides in which the alkyl radicals are independently straight or branched (C1 -C4) alkyl groups such as tetramethylammonium, tetraethylammonium or trimethylethylammonium, as well as trimethylbenzylammonium, triethylbenzylammonium and trimethyl-2-methyl.

Sulfonium and sulfoxonium cations are understood to be the —SH3 and —S (O) H3 cations in which one or more hydrogen atoms may be replaced by organic radicals, for example the above hydrocarbon radicals for organic nitrogen bases.

The radical Q as a straight or branched aliphatic radical having 1 to 5 carbon atoms means non-cyclic, saturated or olefinically unsaturated, aliphatic hydrocarbon radicals, said number of carbon atoms comprising the substituents A, E, G, L, M, A ', E' , G ', L * and M' only in so far as they are optionally substituted alkyl radicals.

If R 1 and G together form a trimethyl ester bridge, a pyrrolidone ring may be used.

Preferred are compounds of formula I which belong to any of the following groups of compounds:

(a) Compounds of formula I wherein X is hydrogen or chlorine;

R 1 represents a hydrogen atom, a nitroso group, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group in the alkyl moiety optionally substituted by at least one halogen atom,

243773

Q represents a straight or branched aliphatic radical having 1 to 5 carbon atoms of the formula

1 * F 1 L · - E 1 -O 1 ‘G and ™ c - } -c- hí 1 • c Me 1 .E. and , b G ' 1 L C 1 к!

X represents a hydrogen atom or a chlorine atom,

R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

Q represents a straight or branched alkylene radical having 1 to 5 carbon atoms of the formula wherein

A ', E', G ', L' and M ^J are hydrogen or C 1 -C 4 alkyl, or two adjacent substituents A, E ', G'. I / and M 'together also form a bond between the two carbon atoms to which they are attached,

A, E, G, L and M are hydrogen or one of the substituents Λ, E, G, L and M are also known on the group -OR ^2, -SR ^3, -COOR ^4, alkyl having 1 to 4 carbon atoms or alkyl (C 1 -C 4) group substituted with -OR ⁵ , -SR ⁶ or -COOR ⁷ , wherein

R ² and R ⁵ are hydrogen,

R ³ and R ⁶ are C 1 -C 4 alkyl and

R ⁴ and R ⁷ are hydrogen or C 1 -C 4 alkyl and a, b, c and d are 0 or 1, or

R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a

Z represents —COO Me Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or —CN, wherein

Me © means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfoxonium cation,

R ⁸ represents a hydrogen atom, a C 1 -C 4 alkyl group optionally substituted by a halogen or a C 1 -C 4 alkoxy group, or a C 2 -C 4 alkenyl group,

R 9 is hydrogen, C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and

R ¹⁰ is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally substituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylaminocarbonyl C 3 -C 6 cycloalkyl, wherein in the compounds wherein R ¹ is hydrogen and a, b, c, and d are each 0, i) G is -COOR ⁴ or C 1 -C 4 alkyl, which is substituted with -OR ⁵ , -SR ⁶ or -COOR ⁷ , or ii) G and G 'are both C 1 -C 4 alkyl.

(b) Compounds of formula (I) wherein:

G

I си

in which

A, E, G, L and M are hydrogen or one of A, E, G, L and M is also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl or C 1 -C 4 alkyl; -OR ⁵ , -SR ⁶ or -COOR ⁷ substituted C 1 -C 4 alkyl, wherein

R ² and R ⁵ are hydrogen,

R ³ and R ⁶ are C 1 -C 4 alkyl and

R ⁴ and R ⁷ are hydrogen or C 1 -C 4 alkyl, a, b, c and d are 0 or 1, or

R ¹ and G together represent a trimethylene bridge, aa, b, c and d are 0, a

Z represents —COO Me Me®, —COOR ⁸ —CONR ⁹ R10 or cyano, wherein:

Me® means a metal cation,

R ⁸ represents a hydrogen atom or a C 1 -C 4 alkyl group;

R ⁹ and R ¹⁰ are hydrogen or C 1 -C 4 alkyl, wherein in the compounds where R ¹ is hydrogen simultaneously, aa, b, c and d are 0, G is -OR ² , -COOR ^4, or (C 1 -C 4) -alkyl substituted with -OR ⁵ , -SR ⁶ or -COOR ⁷ .

c) Compounds of formula I wherein:

X represents a hydrogen atom or a chlorine atom,

R @ ¹ represents a hydrogen atom or a C1 -C4 alkyl group,

Q represents a straight or branched alkylene radical having 1 to 5 carbon atoms of the formula

in which

A _; E, G, L and M are hydrogen or one of A, E, G, L and M is also a group -OR ^2, -SR ^3, -COOR ^4, alkylo245775 hydrocarbyl of 1 to 4 carbon atoms or -OR ⁵ , -SR ⁶ or -COOR ⁷ substituted with an alkyl group having from 1 to 4 carbon atoms ^{; 1} ' ^! taking ^{! л} '·'

R ² and R ⁵ are hydrogen,

R ³ and R ⁶ are C 1 -C 4 alkyl, and

R ⁴ and R ⁷ are hydrogen or C 1 -C 4 alkyl, two a, b, c and d are 0 and the other two are 0 or 1, or

R ¹ and G represent a trimethylene bridge, and a. B, c and d are 0, a

Z is --COO (R) Me, - COOR ( ⁸⁾ or cyano, wherein

Me® means a metal cation,

R ⁸ is hydrogen or C 1 -C 4 alkyl, wherein in the compounds wherein R ¹ is hydrogen and a and b and c are respectively · 0, G is -OR ² , -COOR ^{4, or} -OR ⁵ , - SR ⁶ or -COOR ⁷ substituted C 1 -C 4 alkyl.

d) Compounds of formula I wherein:

X is hydrogen or chlorine,

R ¹ is hydrogen, nitnoso, methyl, methylcarbonyl, ethylcarbionyl, vinylcarbonyl, chloromethylcarbonyl, trichloromethylcarboinyl or trifluoromethylcarbonyl,

Q represents a straight or branched aliphatic radical having 1 to 5 carbon atoms of the formula

R ⁴ and R ⁷ represent hydrogen or alkylp.vou group having 1 to 4 carbon atoms, and * ^3, b, c and d are 0 or 1, or

R ¹ and G _: together they start the ierimethylene bridge and a, b, o and d are 0, and

Z is --COO ® Me, - COOR ⁸ , - CON ⁹ R ¹⁰ or cyano, wherein. _r

Me © means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfoxonium cation,

R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with halogen or C 1 -C 4 alkoxy, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl,

R ⁹ represents hydrogen, an alkyl group of up to 4 carbon atoms or a cycloalkyloxy group of 3 to 6 carbon atoms, and

R ¹⁰ is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally monosubstituted with C 1 -C 4 alkoxy, C 4 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylaminocarbonyl a group having 3 to 6 carbon atoms in the cycloalkyl moiety, wherein in compounds in which R @ ¹ is simultaneously hydrogen and a, b, c and d are 0, i) G is --COOR @ ⁴ or a C1 -C4 alkyl group which: is substituted with -OR ⁵ , -SR ^6, or -COOR ⁷ , or G and G 'are both C 1 -C 4 alkyl.

e) Compounds of formula I wherein:

X is hydrogen or chlorine,

R ¹ represents viodík · or a methyl group,

Q represents a straight or branched alkylene radical having 1 to 5 carbon atoms of the formula wherein

A ', E', G ', L' and M 'denote hydrogen or a C 1 -C 4 alkyl group or two adjacent substituents A \ E \ G', L 'and M' together also represent a bond between the two carbon atoms, to which they are bound,

A, E, G, L, and M are hydrogen or one of A, E, G, L, and M is also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl, or - OR 5, -SR ⁶ or -COOR ⁷ substituted C 1 -C 4 alkyl, wherein

R ² and R ⁵ are hydrogen,

R ³ and R ⁶ are C 1 -C 4 alkyl, and

in which

A, E, G, L and M are hydrogen or one of A, E, G, L and M is also -OR ² -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl, or - OR ⁵ , -SR ⁶ or -COOR ⁷ substituted C 1 -C 4 alkyl, wherein

R ² and R ⁵ are hydrogen,

R ³ and R ⁶ are C 1 -C 4 alkyl, and

R ⁴ and R ⁷ represent hydrogen or an alkyl group having 1 to 4 carbon atoms, two of a, b and c are 0 and the other two are 0 or 1, or

R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a

X is -COO®Me®, -COOR ⁸ or cyano, where

Me® means a metal cation and

R ⁸ is hydrogen or C 1 -C 4 alkyl, wherein in the compounds wherein R ¹ is hydrogen aa, b and c and d are respectively · 0, G is -OR ² , -COOR ^4, or -OR ⁵ , -SR ⁶ or -COOR ⁷ substituted C 1 -C 4 alkyl.

(f) Compounds of formula (I) wherein:

X is hydrogen or chlorine,

R ¹ is hydrogen, nitro or C 2 -C 4 alkyl, C 1 -C 4 alkylcarbonyl optionally substituted with up to 3 chlorine or fluorine atoms, or C 2 -C 4 alkenylcarbonyl in the alkenyl moiety,

Q represents a 1,5-pentamethylene group or a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula

~ A | Г * " E AND G —Ϊ - Γ * and M ~ • o and -whose and - σ- 1 -c- and •C -IN and & .E: ι 6 G ' 1 1 к

in which

A ', E \ G', L 'and M' are hydrogen or one of the substituents A ', E', G 'L' and M 'is also an alkyl group having 1 to 4 carbon atoms or two adjacent substituents A', E ', G', L 'and M * also together represent a bond between the two carbon atoms to which they are attached,

A, E, G, L and M are hydrogen or one of A, E, G, L and M is also a carboxyl group, a C 1 -C 4 alkoxycarbonyl group, a C 1 -C 4 alkyl group, which is optionally monosubstituted by hydroxy or C1 -C4 alkylthio, two of the symbols a, b, c and d being 0 and the remaining two being »0 or 1, or

R ¹ and G together are a trimethylem bridge, aa, b, c and d are 0, a

Z represents a group - COO®Me®, COOR ⁸ , —CONR ⁹ R ¹⁰ or a cyano group, wherein

ME® represents an alkali metal cation, ^R8 is hydrogen, alkyl having 1 to 4 ato »we alkyl optionally nosubstitu him, alkylated or chlorine alkoxyskupinoiu having 1-4 carbon atoms, alkenyl having 2 to 4 carbon atoms or an alkynyl (C 3 -C 4) group;

R ⁹ is hydrogen, C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and

R ¹⁰ represents hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally monosubstituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylaminocarbonyl; C 3 -C 6 carbon atoms in the cycloalkyl moiety, wherein in compounds wherein R ¹ is hydrogen simultaneously, aa, b, c and d are 0, i) G is carboxyl, C 1 -C 4 alkoxycarbonyl, alkyl or (C 1 -C 4) alkyl which is monosubstituted by hydroxy or (C 1 -C 4) alkylthio; or (ii) G and G 'are both C 1 -C 4 alkyl.

g) Compounds of formula I wherein X is hydrogen,

R ¹ represents hydrogen,

Q represents a 1,2-ethylene bridge and

Z represents —COO®Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or cyano, wherein:

ME® is an ammonium cation, a metal cation, a cation of an organic nitrogen base, sulfonium cation or sulfoxcniový kaťont, ^R8 is hydrogen, alkyl having 1 to 4 atiomy atoms which is optionally monosubstituted by halogen, cyano or alkoxy having 1 to 4 carbon atoms, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl;

R ⁹ is hydrogen, (C 1 -C 4) alkyl or (C 3 -C 6) cycloalkyl; and

R ¹⁰ is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally monosubstituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylaminocarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety.

h) Compounds of formula I wherein X is hydrogen or chlorine,

R ¹ represents hydrogen _я nitroso group or an alkyl group having 1-4 carbon atoms, alkenyl having 2 to 4 carbon atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety which is pio case substituted by at least one halogen atom, or represents an alkenylcarbonyl (C 2 -C 4) alkenyl moiety,

Q represents a 1,5-pentamethylene group or represents a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula

in which

A \ E ', G, ^T, L' and M 'are hydrogen or one of A', E ', G', L 'and M' is also a methyl group or two adjacent substituents A ', E', G \ L 'and M' together also mean a bond between the two carbon atoms to which they are attached,

A, E, G, L, and M are hydrogen or one of A, E, G, L, and M is also carboxyl, methoxycarbonyl, ethoxycarbonyl, methyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyoxyethyl or 2-methylthtoethyl, two of a, b, c and d are 0 and both are 0 or 1, or

R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a

Z represents —COO®Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or cyano, wherein:

Me® means sodium cation,

R ⁸ represents hydrogen, (C 1 -C 4) alkyl, 2-chloroethyl, (10) U, 2-methoxyethyl, allyl or 2-propynyl,

R ⁹ is hydrogen, methyl or cyclohexyl; and

R ¹⁰ represents hydrogen, amino, hydroxy, C 1 -C 3 alkyl, 2-methoxyethyl,

3-butin-2-yl, methoxy or cyclohexylaminocarbonyl, wherein in compounds wherein R ¹ is hydrogen and a, b, c and d are 0, i) G is carboxyl, methoxycarbonyl, ethoxycarbonyl, hydroxymethyl, 1-hydroxyethyl,

2-hydroxyethyl or methylthioethyl; or ii) G and G oba are both methyl.

(i) Compounds of formula (I) wherein:

X is hydrogen or chlorine,

R ¹ is hydrogen, nitroso, C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl optionally substituted with 1 to 3 chlorine or fluorine atoms or C 2 -C 4 alkenylcarbonyl in the alkenyl moiety,

Q represents a 1,5-pentamethylene group or a straight or branched aliphatic group

in which

A \ E ', G', L 'and M' are hydrogen or one of A ', E', G ', L' and M ^t is also an alkyl group having 1 to 4 carbon atoms or two adjacent substituents A ' E ', G' L 'and M' together also represent a bond between the two carbon atoms to which they are attached,

A, E, G, L and M are hydrogen or one of A, E, G, L and M is also carboxyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkyl, which is optionally monosubstituted with hydroxy or (C 1 -C 4) alkylthio, two of a, b, c and d are 0 and both of which are 0 or 1, or

R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a

Z represents a group —COO®Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or —CN, wherein

Me® means an alkali metal cation,

R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with chlorine or C 1 -C 4 alkoxy, or C 2 -C 4 alkenyl,

R ⁹ is hydrogen, (C 1 -C 4) alkyl or (C 3 -C 6) cycloalkyl; and

R ¹⁰ is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally monosubstituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, or cycloalkylaminocarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, wherein in compounds in which R ¹ is hydrogen aa, b, c and d are 0, i) G is carboxy, C 1 -C 4 alkoxycarbonyl an alkyl group having 1 to 4 carbon atoms, which is monosubstituted with a hydroxy group or an alkylthio group having 1 to 4 carbon atoms, or G and G ¹ are both alkyl having 1 to 4 carbon atoms.

k) Compounds of formula I wherein:

X is hydrogen or chlorine,

R ¹ represents hydrogen, nitroookspuinu, methyl, methylcarbonyl skupenu, ethylcarbonyl, vinylcarbonyl group, chlormethylkarbonylovou group trichlormethylkarboinylovou trifluormethylkarbonylovou group or radical,

Q represents a 1,5-pentamethylene group or a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula: a group, a methoxycarbonyl group, an ethoxycarbonyl group, a hydroxymethyl group, a 1-hydroxyethyl group,

2-hydroxyethyl or 2-methylthioethyl; or ii) G and G ‘are both methyl.

(1) Compounds of formula (I) wherein X is hydrogen or chlorine,

R ¹ represents hydrogen, nitroso, methyl, methylcarbonyl, ethylcarbonyl, chlormethylkarbonylovou group trichlormethylkarbonylovou group trifluoirmethylkarbonylovou group,

Q represents a 1,5-pentamethylene group or represents a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula

’A 1 ( E AND G AND ~ L ~ F M J -οι 1 - Ο- Ι 1 -c- and 1 c L ..ej G' 1 < 1

Г Ί AND and ~ E ~ 1 G 1 L < X ”X M ( O 1 - ·· o! and - 1 1 -C- AND • c · ..fd 1 b G 1 к

in which

A \ E ', G', L 'and M' are hydrogen or one of A ', E', G ', L' and M 'is also methyl or two adjacent substituents A', E ', G', L 'and M' together also represent a bond between the two carbon atoms to which the substituents are attached,

A, E, G, L, and M are hydrogen or one of A, E, G, L, and M is also carboxyl, methoxycarbonyl, ethoxycarbonyl, methyl, hydroxymethyl, 1-hydroxyethyl, 2- hydroxyethyl or 2-methylthioethyl, two of the symbols a, b, c and d are the number · 0 and both are 0 or 1, or

R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a

Z represents —COO Me Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or —CN, wherein

Me ® means sodium cation,

R ⁸ is hydrogen, C 1 -C 4 alkyl, 2-chloroethyl, 2-methoxyethyl, allyl or 2-propynyl,

R ⁹ is hydrogen, methyl or cyclohexyl; and

R ¹⁰ is hydrogen, amino, hydroxy, C 1 -C 3 alkyl, 2-methoxyethyl, 3-butin-2-yl, methoxy or cyclohexylaminocarbonyl, wherein in the compounds wherein R ¹ is simultaneously hydrogen and a, b, c and d are 0; i] G is carboxyl in which

A 'and E \ G', L 'and M' are hydrogen or one of A \ E ', G', L 'and M ^z is also methyl, or two adjacent substituents A ^C, E', G ', L and together also represent a bond between the two carbon atoms to which these substituents are attached,

A, E, G, L and M are hydrogen or one of the substituents A, E, G, L and M are also carboxy ethoxycarbonyl, methyl, hydroxymethyl, 1-hydroxyethyl or 2-methylthioethyl, two of a, b, c and d are 0 and both are 0 or 1, or

R ¹ and G together represent a trimethylene bridge and a. B, c and d are 0, a

Z is -COOR ³ , -CONR ⁹ R ¹⁰ or-CN, wherein

R ⁸ is hydrogen, C 1 -C 4 alkyl, 2-chloroethyl, 2-methoxyethyl or allyl,

R ⁹ is hydrogen, methyl or cyclohexyl; and

R ¹⁰ represents hydrogen, amino, hydroxy, C 1 -C 3 alkyl, 2-methoxyethyl,

3-butin-2-yl, methoxy or cyclohexylaminocarbonyl, wherein in compounds wherein R ¹ is hydrogen aa, b, c and d are 0, i) G is carboxyl, ethoxycarbonyl, hyd245775

1S roxymethyl, 1-hydroxyoxyethyl or 2-methylthioethyl or 1 G and G 2 are both methyl.

m) Compounds of formula I wherein X is hydrogen,

R1 is hydrogen or methyl,

Q represents an alkylene radical having 1 to 3 carbon atoms of the formula

AND

CHh-CH in which

A, E, G, L and 'M are hydrogen or one of A, E, G, L and M is also methyl, hydroxymethyl, 1-hydroxyethyl or 2-methylthirethyl, two of and, b, c and d are the number · 0 and both others are the number · 0 or 1, or

R1 and G together represent Ιι ^ θ ^^ π) the junction a, b, c and d represent the number 0, and

Z is -COOH, -COO-C1-C4 alkyl, -COO-CH 2 -CH 2 O-CH 3 or -CN, wherein in the compounds in which, simultaneously, R ¹ is hydrogen and a, b, c G = hydroxymethyl, 1-hydroxyethyl or 1 · 2-methylthioelyl.

(n) Compounds of formula (I) wherein:

X is hydrogen,

R ¹ represents hydrogen,

Q represents an ethylene or trimethylene bridge and

Z is --COOR ⁸ or - CONR ⁹ R ¹⁰ , wherein

R ⁸ is hydrogen, C 1 -C 3 alkyl or allyl;

R ⁹ and R 10 are hydrogen.

Particularly preferred compounds are: N- [2-nitro-5- methyl ester

- (2-chloro-4-trifluoromethylphenoxy} phenyl) -3-aminopropionic acid, methyl N- [2-nitro-10-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -4 -amino-n-butyric acid, N- [2-piperidyl-

- (2-chloro-4-trifluoromethylphenoxy) phenyl) -3-aminopropionic acid, ethyl N- [2-nitro-5-

- (2-chloro-4-trifluoromethylphenoxy) phenyl) -3-aminopropionic acid.

N- [2-piperidin-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropyric acid,

N- [2-nitro-5- [2-chloro-4-trifluoromethyl-phenoxy) -phenyl] -4-amino-n-butyric acid amide-3- [N- (2-nitro-5- / 2-chloro) -amide 4-Trifluoromethylphenoxy / phenyl) amino] propionic acid and N- [2-nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropionic acid allyl ester.

The present invention therefore provides a composition for controlling weeds and / or for desiccating and / or defoliating cotton and potato plants, characterized in that it contains at least one compound of the formula I as active ingredient.

Cl (I) wherein

X is hydrogen or chlorine

R1 represents a hydrogen atom, a pilroso group or a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkylcarbonyl group optionally substituted by at least one halogen atom or an alkenylcarbonyl group; C 2 -C 4 alkenyl in the first part,

Q stands for straight or branched alipha-

in which

A ', E', G ', L' and M 'both represent hydrogen or a C 1 -C 4 alkyl group or two adjacent substituents A', E ', G', L 'and M' together also represent a bond between the two the carbon atoms to which they are attached,

A, E, G, L and M are hydrogen or one or two of A, E, G, L and M are also -OR 2, -SR 3 -COOR ⁴ , C 1 -C 4 alkyl · or a group -OR ^5, -SR ⁶ or -COOR ⁷ substituted alkyl group having 1 to 4 carbon atoms, and

R ² and R ⁵ are hydrogen,

R ³ and R ⁶ are C 1 -C 4 alkyl, and

R ⁴ and R ⁷ represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, a, b, c and d are 0 or 1, or

R ¹ and G together are a trimethylenium bridge and a, b and c are 0, a

Z represents —COO®Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or a cyano group, wherein:

Me® means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfoxonium cation,

R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with halogen, cyano or C 1 -C 4 alkoxy, furthermore C 2 -C 4 alkenyl or; (C 3 -C 4) alkynyl,

R ⁹ represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 3 -C 6 cycloalkyl group; and

R ¹⁰ is hydrogen, anťnoskupinu hydroxy, alkyl having 1 to 4 carbon atoms which is optionally monosubstituted alkioxyskupinou having 1-4 carbon atoms, alkynyl having 2 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or cykloalkylaminokarbonylovou group C 3 -C 6 cycloalkyl moiety, wherein in compounds wherein R ¹ is hydrogen and a, b, c and d are 0, i) G is -OR ² , -COOR ^4, or C 1 -C 4 alkyl which is substituted with OR ⁵ , -SR ⁶ or -COOR ⁷ , or ii) G and G 'are both C 1 -C 4 alkyl.

According to the invention, the compounds of formula (I) are produced by producing a compound of formula (IJ)

in which

X is as defined for Formula I, reacted with a compound of Formula III

Ri

AND

HN — Q — Z (ΠΙ) in which

R ^1, Q and Z have the meanings given for formula I in the presence of a base, and optionally the obtained compound of the formula · I in which Z at a respective derivatives karbobcylové acid.

The process according to the invention will hereinafter be referred to as process (variant) a).

In addition to the process of the invention, the compounds of formula (I) may be prepared by:

b) a compound of formula IV

in which

X is as defined for formula I and

D is a leaving group, reacted with a compound of formula III

R ¹

AND

HN — Q — Z (ΠΙ) in which

R ^1, Q and Z have the meanings given for vzoirec I, or

c) reacting a compound of the formula V in order to prepare compounds of the formula I in which R @ ¹ represents a C1 -C4 alkylcarbonyl group;

in which

X, Q and Z have the meanings given for formula I and

T is hydrogen or nitro, with acid anhydride or acid chloride, and when T is hydrogen, the reaction product obtained is nitrated, or

d) to a compound of formula VII

(VII) in which:

X is as defined for Formula I and Hal is a halogen atom, acts by a compound of Formula VIII

in which

R1, Q and Z have the meanings given for formula I in the presence of a base at elevated temperature, whereupon the reaction product of formula IX obtained

in which

X, R ¹ , Q and Z have the meanings given for formula I, nitrates, or is

e) reacting a compound of formula V in which X, Q, Z and T are as defined above with a corresponding alkylating agent to produce compounds of formula I wherein R ¹ is C 1 -C 4 alkyl; and

optionally, the obtained compounds of formula I in which Z is a carboxyl group are converted to the corresponding carboxylic acid derivatives.

The starting compounds of the formulas II, III, IV, V, VI, VII, VIII and IX are known or can be prepared in analogy to known processes.

The reactions according to the invention as well as according to process variants b), c), d) and e) can be carried out without or in the presence of inert solvents or diluents which are inert to the reactants. Preferred are organic solvents such as low molecular weight alcohols, ketones such as methyl ethyl ketone or dimethylformamide, dimethyl sulfoxide or chlorinated hydrocarbons, ethers or aromatic hydrocarbons.

The reaction temperatures are between 0 and 200 degrees Celsius, preferably in the range of 20 to 100 ° C.

Suitable bases are, for example, potassium hydroxide, sodium methoxide, potassium carbonate, potassium tert-butoxide or organic bases such as triethylamine.

Suitable leaving groups D in process variant b) are, for example, halogen, methoxy, 2-chloro-4-trifluoromethylphenoxy or

2,6-dichloro-4-trifluoromethylphenoxy.

Suitable alkylating agents are the corresponding alkyl halides or alkyl sulfates.

The nitration of the reaction product of the formula IX is carried out in a manner known per se by treatment with conventional mixtures of nitrating acid. As such, for example, mixtures of concentrated sulfuric acid and nitric acid or concentrated sulfuric acid and alkali metal nitrate salts may be used.

For application as herbicides, desiccants or defoliating agents, the compounds of the formula I are used in unchanged form or preferably together with auxiliaries which are customary in the manufacture of such compositions and are therefore processed, for example, into emulsion concentrates, pastes which can be applied by coating, to directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, also encapsulated in, for example, polymeric substances in a manner known per se. Methods of application, such as spraying, fogging, dusting, sprinkling, coating or potting, as well as the type of compositions, are selected in accordance with the desired objectives and conditions.

The compositions, i.e. compositions, preparations or mixtures containing the active compound of the formula I and optionally a solid or liquid carrier, are prepared in a known manner, for example by thoroughly mixing and / or grinding the active compounds with fillers such as solvents, solid carriers and optionally surface active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably C8-C12 fractions, such as mixtures of xylenes or substituted naphthalenes, phthalic acid esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffinic hydrocarbons, alcohols and glycols such as 1; their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone. dimethylsulfoxide or dimethylformamide, as well as optionally epoxidized vegetable oils such as. epoxidated coconut oil or soybean oil, or water.

As solid carriers, for example for dusts and dispersible powders, natural stone flours such as limestone, talc, kaolin, montmorillonite or attapulgite are generally used. Highly dispersed silicic acid or high dispersed absorbent polymers may also be added to improve physical properties. Suitable granular adsorptive carriers for the granulate are porous types, such as pumice, brick pulp, sepiolite or bentonite, and non-sorptive carrier materials, for example limestone or sand. In addition, a number of pre-granulated materials of inorganic or organic nature, such as in particular dolomite or comminuted plant residues, may be used.

Depending on the type of active compound of the formula I to be formulated, nonionic, cationic and / or anionic surfactants having good emulsifying, dispersing and wetting properties are suitable as surface-active compounds. Surfactants are also understood as meaning mixtures of surfactants.

Suitable anionic surfactants can be both so-called water-soluble soaps, such as water-soluble synthetic surface-active compounds.

Soaps include alkali metal, alkaline earth metal, or optionally substituted ammonium salts of higher fatty acids (C 10 -C 22), or sodium or potassium salts of oleic acid or ¹ acid, or the corresponding salts of natural fatty acid mixtures which may be obtained, for example, from coconut oil or tallow. Fatty acid salts of methyl taurine must also be mentioned.

However, so-called synthetic surfactants, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates, are more commonly used.

Fatty sulfonates or fatty sulfates are generally present as alkali metal, alkaline earth metal or optionally substituted ammonium salts and contain an alkyl radical of 8 to 22 carbon atoms, the alkyl also including the alkyl portion of the acyl radicals, such as sodium or calcium salt. ligninsulphonic acid, dodecylsulphuric acid ester, or a mixture of sulphated fatty alcohol produced from natural fatty acids. Also included are salts of sulfuric acid esters and sulfonic acids derived from ethylene oxide adducts with fatty alcohols. The sulfonated benzimidazole derivatives preferably contain two sulfo groups and a C 8 -C 22 fatty acid residue. Alkylarylsulfonates are, for example, sodium, calcium or triethanolammonium salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or the naphthalenesulfonic acid-formaldehyde condensation product.

Also suitable are the corresponding phosphates, such as, for example, salts of the phosphoric acid ester adduct of 4 to 14 moles of ethylene oxide with p-nonylphenol.

Suitable nonionic surfactants are, in particular, derivatives of polyglycol ethers of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which may contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the [aliphatic] hydrocarbon radical and 6 to 18 atoms carbon in the alkyl radical of alkylphenols.

Other suitable nonionic surfactants are the adducts of polyethylene oxide and polypropylene glycol, ethylenediaminopalypropylene glycol and an alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain, which are water-soluble and containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. Said compounds usually contain 1 to 5 units of ethylene glycol per propylene glycol unit.

Examples of nonionic surfactants include nonylphenolpolyethoxyethanols, castor oil glycol ethers, polypropylene and polyethylene oxide adducts, tributylphenoxypolyethoxyethaniol, polyethylene glycol and octylphenoxypolyethoxyethanol.

Also suitable are polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are in particular quaternary ammonium salts which contain at least one C 8 -C 22 alkyl radical on the nitrogen and, as further substituents, lower or halogenated alkyl radicals, benzyl radicals or lower hydroxyalkyl radicals. These salts are preferably present as halides, methylsulfates or ethylsulfates, for example stearyltrimethylammonium chloride or benzyl-di (2-chloroethyl) ethylammonium bromide.

Surfactants useful in the preparation of compositions are described, inter alia, in the following publications:

Mc Cutcheon's Detergents and Emulsifiers Annual MC Publishing Corp., Ringwalod, New Jersey, 1980

Sisely and Wood, &quot; Encyclopedia of Surface Active Agents &quot;, Chemical Publishing Co., Inc. New York, 1980.

The agrochemical compositions generally contain 0.1 to 99%, in particular 0.1 to 95%, of the active compound of the formula I, 99.9 to 1%, in particular

99.8 to 5% solid or liquid additives and 0 to 25%, in particular 0.1 to 25%, surfactants.

24577S

While concentrated products are preferred as market goods, the end consumer generally uses dilute products.

Said compositions may also contain other additives, such as stabilizers, anti-foaming agents, viscosity regulators, binders, adhesives as well as fertilizers or other active substances to achieve special effects.

The novel compounds of the formula I have herbicidal, in particular markedly selective, herbicidal activity against weeds in the stands of various, preferably monocotyledonous crop plants. Wheat, barley, rye, oats, millet, maize and rice are particularly suitable as monocotyledonous crops, the effects in wheat, barley and rice crops being emphasized.

The active compounds can be used pre-emergence or post-emergence to control weeds.

The compounds of the formula I or compositions containing them are particularly suitable for the piostemergence control of weeds in soybean crops. A very particularly preferred field of application, however, is the selective control of weeds, especially dicotyledonous weeds, in cereal crops, particularly in pre-emergence but also in post-emergence application. Particularly preferred in this context are those compounds in which X and R @ 1 are hydrogen, Q is an ethylene or trimethylene bridge and Z is --COOR @ ³ or - CONR @ ⁹ R @ ¹⁰ , wherein R @ ⁸ is hydrogen or a C1 -C3 alkyl group carbon and R 9 and R 10 are hydrogen, especially N- [2-nitro-5- methyl ester.

- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropionic acid, N- [2-methyl-5-

- (2-chloro-4-trifluoromethylphenoxy) phenyl] -4-amino-n-butyric acid, N- [2-nitro-5- isopropyl ester

- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropionic acid, N- [2-nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropionic acid ethyl ester, N- [2-nitro-5-

- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropionic acid,

N- [2-nitro-5-

- [2-chloro-4-trifluoromethylphenoxy] phenyl] -4-amino-n-butyric acid and 3- [N- (2-nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl) amide. amino] propionic acids.

Furthermore, the compounds of formula I and compositions containing them are excellent for desiccating and defoliating cotton and potato plants. The treatment of these ¹ plants is carried out before harvest, the exact moment being dependent on various factors such as the age and condition of the plants and the climatic conditions. Suitably, the treatment of the plants is carried out two weeks before harvest. Especially suitable for. the compounds of formula (I) in which X and R @ ¹ are hydrogen, Q is an ethylene or trimethylene bridge and Z is a methoxycarbonyl or allyloxy group, in particular N- [2- ^; nitro-5-

- (2-chloro-4-trifluoromethylphenoxy) phenyl] -4-amino-n-butyric acid, N- [2-nitro-5-

- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropionic acid and N- [2-nitro-5-

- (2-chloro-4-trifluoromethylphenoxy] phenyl] -3-aminopyridine ^ι ropiorové acid.

Example 1

N- [2-nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -4-amino-n-butyric acid (Compound No. 1) g 3,4-dinitro-2'-chloro-4 Trifluoromethyldiphenyl ether is stirred in 2 ml of dimethylsulfoxide, 3 ml of water, 5.1 g of 4-amino-n-butyric acid and 5 ml of 3% sodium hydroxide, and briefly warmed to 11 DEG to complete the exothermic reaction. The reaction mixture is then poured into about 5 ml of water and extracted once with about 1 ml of toluene, and the aqueous phase thus purified is acidified with glacial acetic acid and extracted several times with ethyl acetate. Of hexane to give 9 g of N- [2-methyl-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -4-amino-n-butyric acid in crystalline form Mp 126-127 ° C.

Example 2

N- [2-Nitrio-5- methyl ester

- (2-chloro-4-trifluoromethylphenoxy) phenyl] -4-amincone-butyric acid (compound 2) g N- [2-nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] - 4-Amino-n-butyric acids were dissolved in 5 ml of methanol, 1 ml of concentrated sulfuric acid was slowly added and the reaction mixture was allowed to stand for several hours. The reaction mixture was then poured onto ice, basified with sodium hydroxide and extracted with toluene. The toluene extract is washed with water until neutral, concentrated in vacuo and then hexane is added. 6 g of N- [2-nitro-5- (2-chloro-4-trifluoromethyl-phenyl) -pheroxy] -4-amiro-β-butyric acid methyl ester is obtained in crystalline form, m.p.

Example 3 g- [N- (2-methyl-5- / 2-ch) or-4245775

-trifluoromethylphenoxy / phenyl) amine]] pnopionamide (compound n. 33) g N- [2-nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-aminopropionic acid (compound n. 33) (3) are introduced in 500 ml of methylene chloride together with 34,3 ml of triethylamine at - 25 ° C. While stirring, 22.8 ml of chloroformic acid ethyl ester are allowed to flow for 30 minutes and the reaction mixture is further stirred at a temperature of -10 to -20 ° C. 40 ml of concentrated ammonia solution are added over two hours and the reaction mixture is allowed to warm to room temperature. The mixture was washed with water and the organic phase was evaporated. The residue was recrystallized from ethyl acetate / hexane. Mp 137-138 ° C.

Example 4

N-acetyl-N- [2-nitro-5- (2-chloro-4-trifluoromethyl-phenoxy) -phenyl] -4-amino-n-butyric acid methyl ester (Compound No. 54) g of N- [2- nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -4-imino-n-butyric acid (Compound No. 2) was refluxed in 30 mL acetyl chloride until evolution of hydrogen chloride ceased. Excess acetyl chloride was removed in vacuo. The title compound is obtained in quantitative yield. n _D = 1.5437.

Example 4a

N- [2-nitno-5- (2-chloro-1-trifluoromethylphenoxy) phenyl] -3-amino-n-propionic acid (Compound No. 3)

53.5 g of 3-amino-n-propionic acid are dissolved in 500 ml of dimethylsulfoxide, 75 ml of water and 34.5 g of potassium hydroxide. 108.8 g of 3,4'-dinitro-2'-chloro-4'-trifluoromethyldiphenyl ether and 18 g of urea are then added with stirring. After 20 hours, the reaction mixture was diluted with 2 L of water and then extracted twice with 200 mL of carbon tetrachloride. The aqueous phase is acidified with concentrated hydrochloric acid and the residue is concentrated to dryness. There was obtained 107 g of N- [2-nitro-5- (2-chloro-4-trifluoromethylphenoxy) phenyl] -3-amino-n-propoonic acid, m.p. 103-105 ° C.

Example 4b

N- [nitroso- (2-nitro-5- / 2-chloro-4-trifluoromethylphenoxy / phenyl)] -3-amino-n-propionic acid [Compound No. 38]

In the same manner as described in the preceding example, the starting materials are mixed with each other, but without the addition of urea. The reaction mixture was diluted with 1 liter of water and then extracted twice with carbon tetrachloride. The aqueous phase is acidified with stirring by adding concentrated hydrochloric acid (dropwise). The residue was dissolved in ethyl acetate. The solution was concentrated by evaporation and the residue was recrystallized from ethyl acetate / hexane. In addition to minor amounts of N- [2-nitro-5- (2-chloro-4-trifluoromethylpheno) (Compound No. 3), N- [nitroso- (2-nitxy) phenyl] -3-amino-n- (5- (2-Chloro-4-trifluoromethyl-phenoxy) -phenyl) -3-amino-n-propionic acid, m.p.

Example 4c

4- [N- (2-iniro) 572-chloro-4-

- trifluoromethylphenoxy (phenyl) amino] -N-isopropyl-n-butyramide (Compound No. 34), and

4- (N- - 2-miro-5- / 2-chloro-4-

-trifluoromethylphenoxy / phenyl) amino · -] / N-Dicyclohexyl-N- (cyclohexylaminocarbonyl) -n-bbutyramide (Compound No. 58) g of dicyclohexylcarbodiimide is added to 10 g of N - [- methyl-5 - (- chloro-4-trifluoromethylphenoxy) phenyl] -4-am; No-n-butyric acids in 100 ml methylene chloride. 1.4 g of isopropylamine are then added to this mixture. The reaction mixture is then allowed to stand for several days and then chromatographed on silica gel using ethyl acetate / hexane (1: 2) as the eluent. In almost equal amounts, 4- [N / (- nitro - / - chloro-4-trifluoromethylphenoxy / phenyl) amino] -N-isopropyl-n-butyramide, m.p. 116 DEG-117 DEG C., was obtained; N - (- nitro-5 - [(1-chloro) -4-trifluoromethylphenoxyphenyl) amino] -N-cyclohexyl-N- (cyclohexylaminocarbonyl) -n-butyramide, m.p. 148-149 ° C.

The following compounds of formula I, which are listed in Table 1 together with the compounds of Examples 1 to 4c, can also be prepared in an analogous manner:

Sk 4— * d ca

О о P-ι 0 О оо 0 гЧ см о см О 0 гН AND О 1 ~ Ч I о о гЧ О гЧ ш ю (X 1 0 1 Ьч rs AND СП г-1 со ’ф гЧ оо гЧ гЧ гН <М 1Ό гЧ ио гЧ 1 со СП

Table

тЧ ρϋ

Д Д О Д д д д ООО о о о ООО о о о ООО о о о

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ОООо — о о — о

it д 1 о 1 ем 1 д со AND о 1 1 1 i 1 1 ем Ем ем ем Д Я Е д д д о о О, 1 1 ООО 1111 1 1 СМ СМ 1 1 Ем ем 1111 04 04 N 04 tO Е Я НН Η- | НЧ W W ИН НЧ plays о о. - О о о о о о о о

Ε Ε Е д д ддддддд

X ЕЕ Ε Е

со

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СН — СН2— —COOs.C4H9 n _D ³¹ 1.5633

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4- »ω ο

d '2 «+ Ч

Cf it

οο ιη ιη ιη ω ο Ο O O CO in r4 'Φ СП © о Ο ο © AND 00 © © © AND 1 τ — 1 in ιη ιη ιη ιη ο I © т-Ч гЧ οο 00 rH со см о <to tp 03 см CM 4- ⁵ Ζ 4- » О O Q Q d d ti d 4-> 4- ⁵ 4-J

CM

Ζ ω

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to £ CJ

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O θ

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Examples of compositions for liquid active substances of formula I (% =% by weight)

Example 5

Emulsion concentrates

and) (b) C) the active substance of Table 1 25% 40% 50% calcium dodecylbenzenesulfonic acid 5% 8% 6% castor oil polyethylene glycol ether (36 moles of ethylene oxide) 5% tributylphenylpolyethylene glycol ether (30 mol ethylene oxide) 12% 4% cyclohexanone - 15% 20% mixture of xylenes 65% 25% 20%

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

Example 6

Solutions:

and) (b) C) (d) the active substance of Table 1 80% 10% 5% 95% ethylenglycolmonomethyl- ether 20% - - - polyethylene glycol (molecular weight 400) - 70% - - N-methyl-2-pyrrolidone - 20% - - epoxidized coconut oil - - 1 5% petrol (within temperature range) boiling point 160 to 190 ° C) - - 94% -

These solutions are suitable for use as minimal drops.

Example 7

Granulates: and) (b) the active substance of Table 1 5% 10% kaolin 94% - highly dispersed silicic acid 1% - attapulgit - 90%

The active substance is dissolved in methylene chloride, the solution is sprayed onto a carrier and then the solvent is evaporated off under vacuum.

Example 8

Dust: and) (b) the active substance of Table 1 2% 5% highly dispersed silicic acid 1% 5% talc 97% - kaolin - 90%

By thoroughly mixing the carrier substances with the active substance, a directly usable dust is obtained.

Examples of compositions for solid active substances of formula I (% =% by weight)

Example 9

Wettable powder

a) b) c)

the active substance of Table 1 25% 50% 75% ligninsulfonic acid sodium salt 5% 5% __ sodium lauryl sulfate 3% - 5% sodium diisobutylnaphthalenesulfonate 6% 10% octylphenolpolethylene glycol ether (7 to 8 moles of ethylene oxide) 2% highly dispersed silicic acid 5% 10% 10% kaolin 62 27% -

The active ingredient is mixed well with the ingredients and the resulting mixture is ground well in a suitable mill. A wettable powder is obtained which can be diluted with water to suspensions of any desired concentration.

Example 10

Emulsion concentrate:

Active ingredient from Table 1 10% octylphenolpolyethylene glycol ether (4 to 5 moles of ethylene oxide) 3%

Example 11 dodecylbenzenesulfonic acid calcium salt 3% castor oil piolyglycol ether (35 mol ethylene oxide) 4% cyclohexanone 30% xylene mixture 50%

Emulsions of any desired concentration can be prepared from this concentrate by dilution with water.

and) (b) the active substance of Table 1 5% 8% talc 95% - kaolin - 92% The active ingredient is mixed with carriers is extruded on an extruder and po- and grind on a suitable mill gains the granulate is then dried in a stream of air. dust suitable for application. Example 13 Example 12 Coated granulate Granules prepared by extrusion: 10% the active substance of Table 1 3% the active substance of Table 1 polyethylene glycol (molecular sodium lignin sulphonate 2% weight 200) 3% carboxymethylcellulose 0 ° / o kaolin 94% kaolin 87% The finely divided active substance is in misi- The active ingredient is mixed with the additives. mixture or evenly applied to the kaolin moistened is ground and moistened with water. This mixture polyethylene glycol. In this way to obtain a dust-free coated granulate.

Example 14

Suspension concentrate:

Active ingredient from Table 1 40% ethylene glycol 10% nonylphenolpolyethylene glycol ether (15 moles ethylene oxide) 6% lignsulfonic acid sodium salt 10% carboxymethylcellulose 1%

37% aqueous formaldehyde solution 0.2% silicone oil in the form of 75% aqueous emulsion 0.8% water 32% feminely ground active ingredient is intimately mixed with the ingredients. A suspension concentrate is obtained from which suspensions of any desired concentration can be prepared by dilution with water.

Example 15

Herbicidal effect in pre-emergence application (germination inhibition)

In the greenhouse, immediately after sowing the seeds of the test plants in the sowing dishes, the soil surface is treated with an aqueous dispersion of the active compounds of the formula I obtained from 25% wettable powder. A concentration of 4 kg of active substance per ha is used. The dishes to be sown are kept in a greenhouse at a temperature of 22 to 25 ^° C and 50 to 70% relative humidity. The experiment is evaluated after 3 weeks and the results are evaluated according to the following scale:

= plants do not germinate or are completely dead to 3 = very potent effect to 6 == moderate effect to 8 = slight effect = no effect (as untreated control).

The compounds of formula I show good activity in this test. Thus, against the weeds mustard (Sinapis), scar (Setaria) and chickweed (Stellaria), the following results were obtained for the following compounds:

Table 2

compound no. Sinapis Setaria 1 1 3 2 1 2 3 1 2 4 3 3 5 1 1 6 1 4 8 1 1 9 1 1 10 1 1 11 1 1 12 1 1 13 1 1 14 1 1 15 Dec 2 3 16 1 2 17 1 1 18 3 1 24 1 1 25 1 1 26 1 1 27 Mar: 1 1 28 3 3 29 1 1 31 4 2 32 1 2 33 1 1 34 1 1 38 1 1 39 5 3 40 1 2 41 2 1 42 4 5 43 1 1 44 2 2 45 1 1 46 2 2 48 1 4 49 3 4 50 1 3 54 1 4

Stellaria

Example 16

Herbicidal effect in pre-emergence application (germination inhibition)

Under the conditions of Example 15, a large number of crop plants and weeds were tested using a concentration of 4 kg and 2 kg of active ingredient per hectare. The results are evaluated according to the scale shown in Example 15.

The compounds of formula I show a good selective herbicidal activity in this test. Thus, the following results were obtained with the following compounds:

Table 3

Compound No. 3 experimental plant amount used 4 kg / ha 2 kg / ha barley 9 9 wheat 9 9 maize 9 9 Sorghum hybr. 8 9 dry rice 6 7 Blood-grass (Digitaria sanguinalis) 4 7 Echinochloa crus galii 4 4 soya 6 8 cotton 5 7 abutilon (Abutilon) 1 1 Sida spinosa 1 2 Amaranthus retroflexus 1 1 goosefoot (Chenopodium res.) 1 1 Black Eggplant (Solanum nigrum) 1 1 Ipomoea (Ipomoea) 2 3 mustard (Sinapis) 1 1 Stellaria 1 1 Daisy (Chrysainthemum leuc.) 1 1 Galium aparine 1 2 Viola tricolor 1 1 Veronice sp. 1 1 Compound # 1 Table 4 11 12 13 14 kg / ha 42 4242 42 4 2 4 2 4 2

experimental wheat wheat maize rice Echinochloa c. g.

soy cotton

Abutilon

Chenopodium res.

Ipomoea

Sinapis

Galium aparine

Viola tricolor

9 77

--89

8 67

9 34

8 67

--28

1112

1111

712

1111

1112

1111

9 89

--99

8 77

812

9 78

--22

1111

1111

1411

11

1312

1111

9 99

9 99

9 99

4 69

9 89

6 34

1214

12

1214

1111

3 23

1111

9 89

9 89

6 89

3 24

9 57

3 22

1111

1111

112 2

1111

3 2 3

1111

Compound No. 16 19 25 27 33 38 40

kg / ha experimental plant 4 2 4 2 4 2 4 2 4 2 4 2 4 2 wheat 7 9 9 9 7 8 6 8 3 4 9 9 9 9 maize 9 9 9 9 8 9 3 8 3 5 9 9 9 9 dry rice 7 9 8 9 4 5 7 9 6 7 6 6 7 9 Echinochloa C. g. 7 9 7 8 1 2 1 2 1 2 6 7 8 9 soya 9 9 9 9 7 8 7 8 6 6 7 9 6 7 cotton 9 9 4 6 1 2 2 4 3 4 8 9 4 8 Abutiton 1 2 1 3 1 1 1 1 1 1 1 2 1 1 Chenopodium res. 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Ipomoea 4 7 3 4 1 2 2 7 2 2 3 3 2 6 Sinapis 1 1 1 1 1 1 1 1 1 2 1 1 1 1 Galium aparine 2 4 2 3 2 3 2 3 3 4 1 1 2 3 Viola tricolor 1 1 1 1 1 1 1 1 1 1 1 1 1 1 PiMklad 17 hold at temperature 24 to 26 Noc: 2 ° C and during 45 to 60% relative humidity air. After 15 Dec

The herbicidal effect of the post-emergence application was evaluated and the result was evaluated for contact (herbicide) on the same scale as for pre-emergence treatment (Example Experimental weeds after emergence (at stage 15)).

The compounds of the formula have a 25% effect on the active substances of the formula I obtained, as shown by the following wettable powder, at a dose of 4 kg, effective results: substances per ha for plants and plants se uTable 5

compound no. Setaria So.lanum 1 4 1 2 2 1 3 3 1 4 5 1 5 4 1 6 5 1 7 5 1 8 1 1 9 2 1 10 2 1 11 6 1 12 4 1 13 5 1 14 2 1 15 Dec 3 1 16 3 1 17 3 1 18 4 1 19 Dec 5 1 24 3 1 25 1 1 26 1 1 27 Mar: 4 1 28 4 1

Sinapis Stellaria Phaseolus 1 2 1 1 1 1 1 2 1 3 6 3 1 1 1 1 1 2 1 3 4 1 1 1 2 1 2 1 1 1 1 1 3 1 1 2 1 2 3 1 2 3 1 2 2 1 1 1 1 1 1 2 2 2 1 3 4 1 1 2 1 1 1 1 1 1 1 1 3 1 1 3

compound no. Setaria Solanum Sinapis Stellaria Phaseolus 29 5 1 1 3 4 30 5 1 1 1 2 31 3 1 3 2 3 32 2 1 1 1 3 33 4 1 1 1 5 38 4 1 1 1 2 39 2 1 1 1 1 40 2 1 1 1 1 41 2 1 1 1 1 43 1 1 1 1 1 44 2 1 1 1 2 45 1 1 1 1 3 47 4 1 1 1 3 48 1 1 1 1 2 49 2 1 1 1 2 50 3 1 1 1 2 51 6 2 1 4 4 53 4 1 1 3 2 54 1 1 1 1 1 Example 18 plant weeds, using centrace 0.5 kg effective per 1 ha. You- Herbicidal effect at postemergent application results rated by the scale referred to in

the contact herbicide of Example 15.

The compounds of formula I show good activity in this test, as shown by the following results:

Under the conditions of Example 17, a large number of culture assays are performed

Table 6

Compound number of the test plant: 3 9 11 12 13 27 Mar: 31 32 33 38 39 44 45 47 49 wheat 8 7 9 7 9 9 9 8 9 9 9 7 8 9 8 maize - 5 9 6 7 9 9 6 8 6 8 6 7 6 5 dry rice 9 8 9 6 8 9 9 8 9 9 9 9 9 9 9 soya 6 6 8 6 6 7 8 4 8 6 9 4 6 5 7 Abutilon 1 1 1 1 1 1 2 1 1 2 7 1 1 2 1 Xanthium 4 4 1 1 1 6 4 1 4 1 4 1 1 1 1 Chenopodium res. 3 2 3 1 2 3 3 1 2 3 2 1 1 1 2 Ipiomoea 4 3 1 1 1 5 6 1 3 2 2 1 1 2 1 Sinapis 1 2 2 1 1 4 5 1 3 1 3 1 1 1 1 Galium aparina 4 3 3 1 2 8 4 2 9 2 3 2 1 3 1 Viola tricolor 1 1 1 1 1 1 1 1 2 1 2 1 1 1 1 The compounds of formula I also show 1 ha according to Table 7 s b) 0,25 kg úči nné higher active substance concentrations good se- substances on 1 ha and c] 0.12 kg of active substance ' on Lactic herbicidal effect, as shown by 1 ha for certain substances: following comparison (a) 0,5 kg active substance on Table 7 Compound number 12 32 44 45 49 concentration (variant) and b C and b C and b C and b C and b C

test plants:

wheat corn rice dry soybean

Abutilon

Xanthium

Cheníopodium res. Ipomoea

Sinapis

Galium aparine

Viola tricolor

89

78

78

68

112

111

111

111

111

112

111

89

78

99

77

111

2

111

112

111

2 2

111

88

79

99

79

111

111

2

113

111

24

111

99

78

99

67

2

112

2

112

112

111

111

99

79

99

78

111

111

2 2

111

111

112

111

Example 19

Desiccating and defoliating effect:

In the greenhouse, Delta-Pine cotton plants are grown in pots filled with a mixture of soil and peat. After 12 weeks [onset of flowering], the plants are sprayed with an aqueous preparation of the active compounds of the formula I in an amount corresponding to 150, 300 and 600 g of active substance per ha (spray liquid quantity of 500 liters per ha). Untreated plants serve as controls. The evaluation of the experiment is carried out 14 days after the application of the active compound by determining the defoliation rate (% of leaf dropped) and desiccation (% / drying of leaves left on the plant), each defoliation percentage being included in the desiccation percentage.

The compounds of formula I show good activity in this test, in particular compounds Nos. 2, 8 and 48, as shown in the following table:

Table 8 amount used compound number

g / ha 2 8 48 150 60% 60% 80% defoliation 300 30% 70% 100% 600 70% 50% 100% 150 80% 80% 100% desikace 300 90% 90% 100% 600 90% 90% 100% The above compounds were have also shown when appropriate try « 5 plants

potatoes as particularly active.

Claims (14)

A composition for weed control and / or desiccation and / or defoliation of cotton and potato plants, characterized in that it contains at least one compound of the formula I ct (I) as an active ingredient in which: X is hydrogen or chlorine, R ¹ represents a hydrogen atom, a nitro group or a C 1 -C 4 alkyl group, a C 2 -C 4 alkenyl group, a C 1 -C 4 alkylcarbonyl group which is, for example, substituted by at least one halogen atom or an alkenylcarbonyl group having 2 to 4 carbon atoms in the alkenyl moiety, Q represents a straight or branched aliphatic radical having 1 to 5 carbon atoms of the formula ~ α ^ί í IN 1 G 1 l t -C- M ~ | 1 - o AND -C- 1 1 - c— C I w 1 Ice 1 Ld 1 l / d in which A ', E', G ', L' and M 'both represent hydrogen or a C 1 -C 4 alkyl group or two adjacent substituents A \ E', G ', L' and M 'also together represent a bond between the two carbon atoms to which they are bound, A, E, G, L and M are hydrogen or one or two of A, E, G, L and M are also a group -OR ^2, -SR ^3, -COOR ^4, alkyl having 1 to 4 atoms or atotny -OR ⁵ , -SR ⁶ or -COOR ⁷ substituted C 1 -C 4 alkyl, wherein R ² and R ⁵ are hydrogen, R ³ and R ⁶ are C 1 -C 4 alkyl, and R ⁴ and R ⁷ represent a hydrogen atom or a (C 1 -C 4) alkyl group, a, b, c and d are a number. 0 or 1, or R1 and G together represent a trimethylene bridge and a, b, c and d represent the number 0, a Z represents a group —COO®Me®, —COOR ⁸ , —CONR ⁹ R10 or a cyano group, wherein Me® means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfoxide cation, R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with halogen, C 1 -C 4 alkoxy, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl , R 9 is hydrogen, C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and R10 is hydrogen, amino, hydroxy, C1-C4alkyl optionally substituted by C1-C4alkoxy, C2-C4alkynyl, C1-C4alkoxy or cycloalkylaminocarboinyl having 3 to 6 carbon atoms in the cycloalkyl moiety, wherein in compounds wherein R 1 is hydrogen simultaneously, aa, b, c and d are 0, i) G is -OR ² , -COOR ^4, or an alkyl group of 1 to 4 carbon atoms which is substituted by oR ^5, -SR 6 or -COOR ^7, or ii) the G and G 'are both alkyl of 1 to 4 carbon atoms. Composition according to Claim 1, characterized in that it contains at least one compound of the formula I as active ingredient, in which: X represents a hydrogen atom or a chlorine atom, R1 represents a hydrogen atom, a nitroso group, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group in the alkyl moiety optionally substituted by at least one halogen atom, Q represents a straight or branched aliphatic radical having 1 to 5 carbon atoms of the formula A ', E', G ', L' and M 'denote hydrogen or a C 1 -C 4 alkyl group or two adjacent substituents A', E ', G', L 'and M' together also form a bond between the two atoms the carbon to which they are attached, A, E, G, L and M are hydrogen or one of A, E, G, L and M is also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl or alkyl (C 1 -C 4) group substituted with -OR 5, -SR 5 or -COOR 7, wherein: R2 and R5 are hydrogen, R 3 and R 6 are C 1 -C 4 alkyl and R4 and R7 are hydrogen or C1-C4alkyl and a, b, c and d are 0 or 1, or R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a Z represents —COO®Me®, —COOR ⁸ , —CONR9R10 or · - CN, wherein: Me® means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfaxonium cation, R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with halogen or C 1 -C 4 alkoxy, or · C 2 -C 4 alkenyl, R 9 is hydrogen, C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and R ¹⁰ represents hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally substituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylam C 3 -C 6 -carbonyl in the cycloalkyl moiety, wherein in compounds in which R 1 is hydrogen simultaneously and a, b, c and d are 0, i) G is -COOR 4 or C 1 -C 4 alkyl; or substituted by -OR 5, -SR 6 or -COOR 7, or ii) G and G 'are both C 1 -C 4 alkyl. 3. A composition according to claim 1, wherein the active ingredient comprises at least one compound of the formula I in which: X represents a hydrogen atom or a chlorine atom, R4 represents a hydrogen atom or a C1-C4 alkyl group, Q represents a straight or branched alkylene dio radical having 1 to 5 carbon atoms of the formula r E G L ~ H 1 1 1 1 1 4 -CH- ^ -CH ~ ^L cw- C _CH _: in which A, E, G, L and M are hydrogen or one of A, E, G, L and M is also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl or -OR ⁵ , -SR ⁶ or -COOR ⁷ substituted C 1 -C 4 alkyl, wherein R2 and R5 are hydrogen, R 3 and R ⁶ are C 1 -C 4 alkyl and R4 and R7 are hydrogen or (C1-C4) alkyl, a, b, c and d are 0 or 1, or R 1 and G together are a trimethylene bridge, and a, b, c and d are 0, a Z is --COO (R) Me, - COOR ( ⁸⁾ , - CONR ( ⁹⁾ R10, or cyano, wherein: Me® means a metal cation, R ⁸ represents hydrogen or alkyl ^gr: comprising 1 to 4 carbon atoms and R ⁹ and R ¹⁰ are hydrogen or C 1 -C 4 alkyl, wherein in the compounds wherein R ¹ is hydrogen simultaneously, aa, b, c and d are 0, G is -OR 2, -COOR ⁴ or -alkyl; group having 1 to 4 carbon atoms substituted by -OR 5, -SR ⁶ or -COOR · ^7th 4. A composition according to claim 1, characterized in that it contains at least one compound of the formula I as active ingredient in which X represents a hydrogen atom or a chlorine atom, · R ¹ is hydrogen or alkyl having 1 to 4 carbon atoms, Q represents a straight or branched alkylene radical having 1 to 5 carbon atoms of the formula wherein A, E, G, L and M are hydrogen or one of A, E, G, L and M is also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl or -OR 5 , -SR ⁶ or -COOR 7 substituted C 1 -C 4 alkyl, wherein R ² and R 5 are hydrogen, R ³ and R 6 are C 1-4 alkyl -a R4 and R7 are hydrogen or (C1-C4) -alkyl, the two symbols a, b, c and d being the number 0-and the remaining two being the number · 0 or · 1, or R ¹ and G together represent a trimethylene bridge, aa, b, c and d are pure 0, and Z is --COO (R) Me, - COOR ( ⁸⁾ or cyano, wherein Me® means a metal cation, R ⁸ is hydrogen or C 1 -C 4 alkyl, wherein in compounds wherein R ¹ is hydrogen and a, b, c, d are 0, G is -OR ² , -COOR ⁴ , or -OR 5 , -SR 6 or -COOR 7 substituted C 1 -C 4 alkyl. 5. A composition according to claim 1, characterized in that it contains at least one compound of the formula I as active ingredient in which: X is hydrogen or chlorine R @ ¹ represents hydrogen, nitrosocycle, methyl, methylcarbonyl, ethylcarbonyl, vinylcarbonyl, chloromethylcarbonyl, trichliomethylcarbonyl or trifluoromethylcarbonyl, Q represents a straight or branched aliphatic radical having 1 to 5 carbon atoms of the formula in which A ', E', G 'L' and M 'represent hydrogen or an alkyl group having 1 to 4 carbon atoms or two adjacent substituents A', E ', G', L 'and M' together also represent a bond between the two the carbon atoms to which they are attached, A, E, G, L and M are hydrogen or one of A, E, G, L and M is also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl, or - OR 5, -SR ⁶ or -COOR 7 substituted C 1 -C 4 alkyl, wherein R ² and R 5 are hydrogen, R ³ and R 6 represents an alkyl group having 1 to 4 carbon atoms, and R ⁴ and R ⁷ represent hydrogen or (C 1 -C 4) -alkyl, a, b, c and d are the numbers · 0 or 1, or R 1 and G together represent a trimethylene bridge and a, b, c and d represent the number -O, and Z is —COO®Me®, —COOR ⁸ , —CONR ⁹ R10, or cyano, wherein: Me © means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfoxonium cation, R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with halo or C 1 -C 4 alkoxy, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl, R ⁹ is hydrogen, (C 1 -C 4) alkyl or (C 3 -C 6) cycloalkyl; and R ^w is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally substituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or a (C 3 -C 6) cycloalkylaminocarbonyl group, wherein in the compounds wherein R ¹ is hydrogen simultaneously and a, b, c and d are 0, i] G is -COOR ⁴ or a C 1 -C 4 alkyl group alkyl which is substituted by -OR ^5, -SR 6 or -COOR 7 group, or ii) the G and G 'represent - both alkyl having - 1 to 4 carbon atoms. б. A composition according to claim 1, characterized in that it contains at least one compound of the formula I as active ingredient in which: X is hydrogen or chlorine, R ¹ represents hydrogen or methyl, Q represents a straight-chain or branched alkylene radical having 1 to 5 carbon atoms of the formula in which A, E, G, L, and M are hydrogen or one of A, E, G, L, and M is also -OR ² , -SR ³ , -COOR ⁴ , C 1 -C 4 alkyl, or - OR ⁵ , -SR ⁶ or -COOR 7 substituted C 1 -C 4 alkyl, wherein R2 and ^R5 are hydrogen, R 3 and R ⁶ are C 1 -C 4 alkyl, and R ⁴ and R 7 are hydrogen or (C 1 -C 4) -alkyl, two of a, b, c -ad are 0 and the remaining two are 0 or 1, or R1 and G together represent a trimethylene bridge and a, b, c and d represent the number 0, a Z represents —COO © Me®, —COOR8, or cyano, wherein Me® means a metal cation and R 8 is hydrogen or C 1 -C 4 alkyl, wherein in compounds wherein R 1 is hydrogen and -a, -b, c, and d are 0, G is -OR ² , -COOR 4, or -OR ⁵ , - SR 6 or -COOR 7 substituted C 1-4 alkyl. 7. A composition according to claim 1, wherein said active ingredient comprises at least one compound of formula (I) wherein: X is hydrogen or chlorine, R ¹ is hydrogen, nitro or C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 alkylcarbonyl optionally substituted with 1 to 3 chlorine or fluorine atoms, or is (C 2 -C 4) alkenylcarbonyl, Q represents a 1,5-pentamethylthio group or a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula A ', - E', G ', - L' and M 'are hydrogen or one of - A', E ', G', L 'and M' is also a C 1 -C 4 alkyl group or two adjacent substituents A ', E', G ', L' and M 'together also mean a bond between - the two carbon atoms to which they are attached, A, E, G, L and M are hydrogen or one of the substituents A, E, G, L and M are also carboxyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkyl, which is optionally monosubstituted by hydroxy or (C 1 -C 4) alkylthio, two of a, b, c and d are 0 and the other two are 0 or 1, or R ¹ and G together represent a trimethylene bridge, aa, b, c and d represent the number · 0, and Z represents a group —C00 Me Me,, —COOR ⁸ , —CONR ⁹ R10 or a cyano group, wherein: Me © means an alkali metal cation, R ⁸ is hydrogen, C 1 -C 4 alkyl optionally substituted with chlorine or C 1 -C 4 alkoxy, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl, R 9 is hydrogen, C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and R 10 represents hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally monosubstituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylaminoalkyl; a (Crb-Crb) -bonyl group in the cycloalkyl moiety, wherein in the compounds in which R R1 is hydrogen at the same time, aa, b, c and d are 00.1; G znamená is carboxyl, a (C,-C alko) alkoxycarbonyl group alkoxy moieties, a (C 1 -C 4) alkyl group monosubstituted with hydroxy or (C 1 -C 4) alkylthio; or (ii) G and G 'are both C 1 -C 4 alkyl. 8. A composition according to claim 1 wherein the active ingredient comprises at least one compound of formula (I) wherein: X is hydrogen, R ¹ represents hydrogen, Q is a 1-ethylene bridge and Z represents -COO Me © © OR8, -CONR9R1 or ⁹ · · CN, Me © means an ammonium cation, a metal cation, an organic nitrogen base cation, a sulfonium cation or a sulfoxonium cation, R 8 is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with halogen, C 1 -C 4 alkoxy, C 2 -C 4 alkenyl or C 3 -C 4 alkynyl, R ⁹ is hydrogen, (C 1 -C 4) alkyl or (C 3 -C 6) cycloalkyl; and R ^w is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally monosubstituted with C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy or cycloalkylaminocarbonyl; C 3 -C 6 cycloalkyl. 9. A composition according to claim 1, wherein the active ingredient comprises at least one compound of formula (I) wherein: X is hydrogen or chlorine, R 1 represents hydrogen, nitro or C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 alkylcarbonyl in the alkyl moiety optionally substituted by at least one halogen atom, or · alkenylcarbonyl having 2 to 4 carbon atoms in the alkenyl moiety, Q represents a SS-pentamethylene group or represents a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula in which: A ', E', G ', L' and M 'are hydrogen or one of A', E ', G', L 'and M' is also methyl · or 'two adjacent substituents A', E ', G ', L' and M 'together also mean a bond between the two carbon atoms to which they are attached, A, E, G, L and M are hydrogen or one of the substituents A, E, G, L and M is also a carboxyl group, a methoxycarbonyl group, a methoxycarbonyl group, a methyl group, a hydroxymethyl group, a 1-hydroxyethoxy group a group, 2-methoxyethyl or 2-methylthioethyl, two of which a, b, c and d are 0 and both of which are 0 or 1, or R1 and G together represent a trimetbylene bridge and a, b, c and d are pure · 0, and Z represents —COO Me Me ©, —COOR8, —CONR9R10 or · cyano, wherein: Me © means sodium cation, R 8 is hydrogen, C 1 -C 4 alkyl, 2-chloroethyl, 2-methoxycarbonyl, allyl or 2-propynyl, R 9 is hydrogen, methyl or cyclohexyl; and R 19 is hydrogen, amino, hydroxy, C 1 -C 3 alkyl, 2-methoxyethyl, 3-butin-2-yl, methoxy or cyclohexylaminocarbonyl, wherein in the compounds wherein R 1 is hydrogen aa, b, c and d are the number · 0, i) G is a carboxyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a hydroxymethyl group, a 1-hydroxyethyl group, 2-Hydroxyethyl or methylthioethyl; or ii) G and G‘ are methyl. . * 10. A composition according to claim 1 as an active ingredient; it comprises at least one compound of general formula (I) in which: X is hydrogen or chlorine, R ¹ is hydrogen, nitrios, C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl in the alkyl moiety optionally substituted with 1 to 3 chlorine or fluorine atoms, or C 2 -C 4 alkenylcarbonyl in the alkenyl moiety, Q represents a 1,5-pentamethylene group or represents a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula in which: A ', E, ^Z, G', L 'and M' are hydrogen or one of A ', E', G ', L' and M 'is also alkyloviou group having 1 to 4 carbon atoms or two adjacent substituents A ¹ 'E', G ', L' and M 'together also represent a bond between the two carbon atoms to which they are attached, A, E, G, L and M are hydrogen or one of A, E, G, L and M is also a carboxyl group, a (C 1 -C 4) alkoxycarbonyl group, a (C 1 -C 4) alkyl group carbon, optionally monosubstituted with hydroxy or (C 1 -C 4) alkyl, two of a, b, c and d are 0 and both are 0 or 1, or R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a Z represents a group - € 00®Me®, —COOR ⁸ , —CONR ⁹ R ¹⁰ or a cyano group, wherein Me® means an alkali cation, R ⁸ is hydrogen, C 1 -C 4 alkyl optionally monosubstituted with chlorine or C 1 -C 4 alkoxy, or C 2 -C 4 alkenyl, R ⁹ is hydrogen, (C 1 -C 4) alkyl or (C 3 -C 6) cycloalkyl; and R ¹⁰ is hydrogen, amino, hydroxy, C 1 -C 4 alkyl optionally substituted by C 1 -C 4 alkoxy, C 2 -C 4 alkynyl, S 1, az ^; (4) carbon atoms or cycloalkylaminocarbonyl having 3 to 6 carbon atoms in the C 1 -C 6 alkyl moiety, wherein in the compound compounds in which R ¹ is hydrogen at the same time, aa, b, c ^: and d are 0, i] G is carboxyl; (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkyl group monoisubstituted with hydroxy or (C 1 -C 4) alkylthio; or (ii) G and G 'are both C 1 -C 4 alkyl groups . 11. A composition according to claim 1, wherein the active ingredient comprises at least one compound of formula (I) wherein: X is hydrogen or chlorine, R ¹ represents hydrogen, nitrcsoskupinu, methyl, methylcarbonyl, ethylcarbonyl, vinylcarbonyl group, chlormethylkarbonylovou group trichlormethylkarbonylovou trifluormethylkarbonylovou group or radical, Q represents a 1,5-pentamethylene group or a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula and and to. | 'G AND L F я j - c- AND -ΟΙ 1 - c- t 1 -c- 1 c A ^f & t 1 b G 1 C; 1 Me in which A ', E, ^C, G', L 'and M' are hydrogen or one of A ', E', G ', L' and M 'is also a methyl group or two adjacent substituents A' and E \ G ^No. L 'and M' together also represent a bond between the two carbon atoms to which the substituents are bonded, A, E, G, L and M are hydrogen or * A, E, G, L and M are also carboxyl, methoxycarbonyl, ethoxycarbonyl, methyl, hydroxymethyl, 1-hydroxyethyl, 2 -hydroxyethyl or 2-methylthioethyl, two of a, b, c and d are 0 and both are 0 or 1, or R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a Z is —COO®Me®, - COOR ⁸ , —CONR ⁹ R ^10, or cyano, wherein: Me® means sodium cation. R ⁸ represents a hydrogen atom, a C 1 -C 4 alkyl group, a 2-chloroethyl group, a 2-methoxyloxy group, an allyl group or a 2-propynyl group, R ⁹ represents a hydrogen atom, a methyl group or a cyclohexyl group and a R ¹⁰ represents hydrogen, amino, hydroxy, C 1 -C 3 alkyl, 2-methoxyethyl, 3-butin-2-yl, methoxy or cyclohexylaminocarbonyl, wherein in compounds wherein R ¹ is hydrogen and a, b, c and d are 0, i) G is carboxyl, methoxycarbonyl, ethoxycarbonyl, hydroxymethyl a 1-hydroxyethyl group, 2-hydroxyethyl or 2-methylthioethyl; or ii) G and G oba are both methyl. 12. A composition according to claim 1, wherein the active ingredient comprises at least one compound of formula (I) wherein: X is hydrogen or chlorine, R ¹ is hydrogen, nitrosio, methyl, methylcarbonyl, ethylcarbonyl, chloromethylcarbonyl, trichloromethylcarbonyl, trifluoromethylcarbonyl, Q represents a 1,5-pentamethylene group or represents a straight or branched aliphatic radical having 1 to 3 carbon atoms of the formula - -, AND 1 E" 1 G | L ' 1 -c- 1 M | 1 - c- -σ- ι 1 c- 1 • c · AND f— л- and- 1 b 1 6 ' 1 "i.e <1 1 in which A ', E', G ', L' and M 'are hydrogen or one of A', E ', G', L 'and M' is also methyl or two adjacent substituents A ', E', G ', L 'and M' are also taken together to represent the bond between the two carbon atoms to which the substituents are attached, A, E, G, L, and M are hydrogen or one of A, E, G, L, and M is also carboxyl, ethoxycarbonyl, methyl, hydroxymethyl, 1-hydroxyethyl or 2-methylthioethyl, two of the symbols a, b, c and d represent the number · 0 and both others represent the number 0 or 1, or R ¹ and G together represent a trimethylem bridge and a, b, c and d are 0, a Z is -COOR ⁸ , CONR ⁹ R ¹⁰ or cyano, wherein R ⁸ is hydrogen, C 1 -C 4 alkyl, 2-chloroethyl ^; a 2-methoxyethyl group or an allyl group, R ⁹ represents a hydrogen atom, a methyl group or a cyclohexyl group and R ¹⁰ represents hydrogen, amino, hydroxy, C 1 -C 3 alkyl, 2-methoxyethyl, 3-butin-2-yl, methoxy or cyclohexylaminocarbonyl, wherein in compounds wherein R ¹ is hydrogen aa, b, c and d are 0, i) G is carboixyl, ethoxycarbonyl, hydroxymethyl, 1-hydroxyethyl or ii) G and G 'are both methyl. 13. A composition according to claim 1, wherein the active ingredient is at least one compound of formula (I) wherein: X is hydrogen, R ¹ represents hydrogen or methyl, Q represents an alkylene radical having 1 to 3 carbon atoms of the formula A 1 1 E 1 G 1 ~ L ' 1 M 1 and. ch- -CH- C in which A, E, G, L and M are hydrogen or one of A, E, G, L and M is also methyl, hydroxymethyl, 1-hydroxyethyl or 2-methylthioethyl, two of a, b, c and d are 0 and both are 0 or 1, or R ¹ and G together represent a trimethylene bridge and a, b, c and d are 0, a Z represents a group - COOH, -COO-alkyl of 1 to 4 carbon atoms in the alkyl - COO - CH 2 - CH 2 - O 2 - or non-CN, wherein in the compounds in which R ¹ is simultaneously hydrogen aa, b, c and d are number · 0, G represents a hydroxymethyl group, a 1-hydroxyethyl group or a 2-methylthioethyl group. 14. A composition according to claim 1, wherein the active ingredient comprises at least one compound of formula I wherein: X is hydrogen, R ¹ represents hydrogen, Q represents an ethylene or trimethylene bridge and